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Aspire Software

Directeur(trice) des ventes – Head of Sales

Aspire Software

. Report to the Managing Director .

Posted 11/12/2026full-timeMontreal • CanadaLeadWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in building and leading sales teams, with a focus on software sales in the healthcare or dental industries. Proficient in utilizing AI for sales processes and achieving revenue targets through effective customer engagement and retention strategies.

Highest-signal resume keywords
Sales Team BuildingSoftware Sales ExperienceAI Utilization in SalesField Sales LeadershipHealthcare Industry Knowledge

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
Sales Playbook DevelopmentPipeline ManagementRevenue OwnershipPerformance MeasurementCustomer Engagement Strategies
Soft Skills
CollaborationLeadershipRecruitmentCommunication
Tools & Technologies
AI AgentsPractice Management SoftwareIntegrated Payments
Industry Keywords
HealthcareDentalPrivate-Equity-BackedTurnaround CompanyOwner-Run Businesses

About the role

Key responsibilities & impact
  • Report to the Managing Director
  • Write the sales playbook covering the ideal customer, messaging, objections, pipeline stages, and rep measurement
  • Recruit the first 2–3 field salespeople, each prospecting in person within a dedicated US territory
  • Build AI agents for pipeline hygiene, rep scorecards, territory maps, commission checks, and other repetitive sales work
  • Own new-logo revenue and expansion across practice management software products
  • Establish daily standards of 3 appointments booked, 2 demos held, and 1 genuine closing opportunity per representative
  • Include integrated payments and AI add-ons in every deal
  • Collaborate with Customer Success to reduce churn and align team compensation with retention
  • Travel as needed to US customers and field representatives

Requirements

What you’ll need
  • Experience building a sales team or sales motion from scratch, ideally at a founder-led, private-equity-backed, or turnaround company
  • Experience recruiting and leading field salespeople who prospect in person and exceed targets
  • Experience selling software, ideally software with payments, to practices or small owner-run businesses
  • Dental or healthcare industry experience is a significant asset
  • Current practical use of AI and ability to demonstrate how it is used